EP0461435B1 - Utilisation d'esters d'acides aromatiques pour compresseur pour machines frigorifiques - Google Patents

Utilisation d'esters d'acides aromatiques pour compresseur pour machines frigorifiques Download PDF

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Publication number
EP0461435B1
EP0461435B1 EP91108312A EP91108312A EP0461435B1 EP 0461435 B1 EP0461435 B1 EP 0461435B1 EP 91108312 A EP91108312 A EP 91108312A EP 91108312 A EP91108312 A EP 91108312A EP 0461435 B1 EP0461435 B1 EP 0461435B1
Authority
EP
European Patent Office
Prior art keywords
esters
refrigerant
lubricants
lubricant
aromatic carboxylic
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP91108312A
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German (de)
English (en)
Other versions
EP0461435A1 (fr
Inventor
Boy Prof. Dr. Dipl.-Chem. Cornils
Jürgen Dr. Dipl.-Chem. Weber
Peter Dr. Dipl.-Chem. Lappe
Helmut Dipl.-Ing. Springer
Ewald Dipl.-Ing. Preisegger
Rainer Dipl.-Ing. Henrici
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Hoechst AG
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Hoechst AG
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Filing date
Publication date
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Publication of EP0461435A1 publication Critical patent/EP0461435A1/fr
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Anticipated expiration legal-status Critical
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M171/00—Lubricating compositions characterised by purely physical criteria, e.g. containing as base-material, thickener or additive, ingredients which are characterised exclusively by their numerically specified physical properties, i.e. containing ingredients which are physically well-defined but for which the chemical nature is either unspecified or only very vaguely indicated
    • C10M171/008—Lubricant compositions compatible with refrigerants
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
    • C10M105/32—Esters
    • C10M105/34—Esters of monocarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
    • C10M105/32—Esters
    • C10M105/36—Esters of polycarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/284—Esters of aromatic monocarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/285—Esters of aromatic polycarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/30—Refrigerators lubricants or compressors lubricants
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/32—Wires, ropes or cables lubricants
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/34—Lubricating-sealants
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/36—Release agents or mold release agents
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/38—Conveyors or chain belts
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/40—Generators or electric motors in oil or gas winning field
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/42—Flashing oils or marking oils
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/44—Super vacuum or supercritical use
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/50—Medical uses

Definitions

  • the invention relates to the use of esters of aromatic carboxylic acids as lubricants for refrigerant compressors which are operated with chlorine-free, partially fluorinated hydrocarbons as refrigerants.
  • Refrigerant compressors are widely used to generate refrigeration in industrial, commercial and private areas. These devices work with mechanical compressors which compress the refrigerant, liquefy in the condenser by cooling with air, water or another medium and evaporate in the evaporator with the absorption of heat from the medium to be cooled.
  • the main refrigerants used are ammonia for large systems and chlorofluorocarbons such as dichlorodifluoromethane, chlorotrifluoromethane for large systems, commercial refrigeration systems and for household appliances.
  • Highly refined, white oil-like, generally naphthenic mineral oils are used to lubricate refrigerant compressors.
  • Alkylaromatics and also polyalpha-olefins are used as fully synthetic oils for refrigerant compressors.
  • the task of the lubricating oils is to lubricate the moving compressor parts, to dissipate the heat from the hot compressor parts and to seal the compression chamber and the valves. These tasks also determine the properties that the lubricating oils must meet. They must be able to withstand thermal loads and remain flowable even at the temperatures of the evaporator. Furthermore, it should be borne in mind that the lubricating oils come from the compression chamber discharged into the refrigerant circuit and cannot be completely removed by downstream oil separators. They must therefore be miscible with the refrigerant over a wide range of temperatures and concentrations, so that the return of lubricating oil that has entered the refrigerant circuit is ensured in the compressor.
  • Chlorofluorocarbons have been suspected for some time of damaging the ozone layer of the earth's atmosphere. Therefore, efforts are being made to limit their use to those cases in which they cannot be replaced. For the rest, one tries to replace them with substances that have the same effect but are harmless.
  • chlorine-free, partially fluorinated hydrocarbons such as 1,1,1,2-tetrafluoroethane, 1,1,1,2,3,3,3-heptafluoropropane, pentafluoroethane, 1,1,1,3, 3,3-hexafluoropropane and trifluoromethane can be used. These materials are characterized by high thermal stability and corresponding thermodynamic properties in the temperature ranges that occur during the operation of refrigerant compressors.
  • polyalkylene glycols can only be used as lubricants to a limited extent because they are highly hygroscopic. Drying them to a residual moisture of ⁇ 100 ppm requires a lot of effort. In addition, care must be taken to ensure that moisture is not absorbed again by completely excluding the air. They can therefore only be used in hermetically sealed, small refrigeration systems, e.g. Household refrigerators. In large refrigeration systems, where maintenance work with occasional interventions in the refrigerant circuit is required, considerable moisture absorption can be expected over time. The moisture bound to the polyalkylene glycol can no longer be removed with the help of filter dryers. This leads to problems with metallic materials in the system. Furthermore, the thermal stability of the polyalkylene glycols does not meet all requirements. Above around 180 ° C, such a temperature can occur in the compressor pressure valve under extreme operating conditions, they begin to decompose.
  • the invention thus consists in the use of esters of phthalic acid, isophthalic acid or terephthalic acid with straight-chain or branched, primary monohydric alcohols with 4 to 20 carbon atoms as lubricants for refrigerant compressors which are operated with chlorine-free, partially fluorinated hydrocarbons as refrigerants.
  • Carboxylic esters derived from aromatic carboxylic acids and monohydric alcohols are widely used as plasticizers for polyvinyl chloride.
  • the property profile required by the carboxylic acid esters for this application differs fundamentally from the features that lubricants for compression refrigeration machines must have. It was therefore not foreseeable that a class of compound that has proven itself particularly in the field of plastics can also be used successfully in a completely different area of technology.
  • Examples of the alcohol component of the esters used according to the invention are n-butanol, isobutanol, n-pentanol, 2-methylbutanol, 3-methylbutanol, 2-ethylbutanol, 2-methylpentanol, n-hexanol, heptanol (in the form of the isomer mixture), octanol (in Form of the isomer mixture), 2-ethylhexanol, n-octanol, i-nonanol, i-decanol, i-tridecanol, i-hexadecanol and i-octadecanol.
  • the branched-chain primary alcohols with at least 4 carbon atoms have proven to be particularly suitable.
  • the alcohols mentioned are obtained predominantly from olefins by oxosynthesis and subsequent hydrogenation of the aldehydes formed or by aldol condensation. All olefins are suitable for oxosynthesis. It usually leads to a mixture of isomeric alcohols. It is not necessary to separate these mixtures to prepare the esters.
  • Suitable esters for use as lubricants are e.g. Di-2-ethylhexl phthalate, di-isononyl phthalate and di-isodecyl phthalate, di-n-butyl phthalate, di-2-ethylhexyl terephthalate, di-isodecyl terephthalate.
  • the esters of phthalic acid e.g. Di-2-ethylhexyl phthalate, di-isononyl phthalate, di-isodecyl phthalate.
  • the esters are prepared in a known manner from the aforementioned acids and alcohols in the presence of acidic catalysts.
  • Mineral acids such as sulfuric acid, phosphoric acid and their acid salts, furthermore trialkyl or triaryl phosphates and p-toluenesulfonic acid are suitable as catalysts.
  • the lubricants used according to the invention have good miscibility with the chlorine-free, partially fluorinated hydrocarbons used as refrigerants, even at -40 ° C., that is to say in the temperature ranges which can occur in compression refrigeration systems.
  • Their viscosity at 40 ° C is between about 10 and 150 cSt and thus corresponds the requirements placed on the lubricant for the area of application described above.
  • They also have excellent thermal stability in the absence of atmospheric oxygen and moisture, that is to say under conditions which must be fulfilled in a refrigerant circuit.
  • the esters are not hygroscopic. They can therefore be dried without much effort. Residual moisture, which may not exceed 35 ppm according to the German standard DIN 51 503, can be easily achieved.
  • esters used as lubricants can be used in pure form, as a mixture of isomeric compounds and as a mixture of two or more esters of different chemical compositions.
  • esters are prepared in the following examples, and their physical properties are also listed insofar as they are important for the use of the esters as lubricants.
  • the scope of the invention is not limited to the described embodiments.
  • the crude ester is neutralized with 5% by weight sodium hydroxide solution, then in the presence of 5% by weight sodium hydroxide solution Distilled at 135 ° C and 150 mbar (15 kPa) over a period of 3 hours with steam and then washed with water. At a pressure of 150 mbar (15 kPa) and 135 ° C, the ester is dried in a stream of nitrogen for 3 hours. After filtration, 362 g of product are obtained, corresponding to a yield of 93%.
  • a mixture of 148 g (1 mol) of phthalic anhydride and 322 g (2.23 mol) of isononyl alcohol is mixed with 70 g of cyclohexane and in the presence of 0.59 g (0.006 mol) of concentrated sulfuric acid, diluted with 1.48 g of water, as Catalyst esterified at 135 ° C over a period of 12 hours.
  • the water of reaction is removed as an azeotrope.
  • the crude ester is first neutralized with 5% by weight sodium hydroxide solution, then distilled over a period of 3 hours at 150 mbar (15 kPa) and 135 ° C. in the presence of 5% by weight sodium hydroxide solution with steam.
  • the ester After washing with water until the neutral point has been reached, the ester is dried in a stream of nitrogen at a pressure of 150 mbar (15 kPa) and a temperature of 135 ° C. for 4 hours. After filtration, 388 g of DINP are obtained, corresponding to a yield of 93%.
  • a mixture of 148 g (1 mol) of phthalic anhydride and 152 g (2.05 mol) of n-butanol is 6 hours at 130 ° after adding 50 g of cyclohexane and 5.7 g (0.03 mol) of p-toluenesulfonic acid as a catalyst C implemented.
  • the water of reaction released during the esterification is removed as an azeotrope.
  • the acidic catalyst contained in the crude ester is first neutralized. After repeated washing with water, the product is dried for 4 hours at a pressure of 150 mbar (15 kPa) and a temperature of 135 ° C. After filtration, 262 g of di (n-butyl) phthalate are obtained, corresponding to a yield of 94%.
  • esters described above as lubricants are their thermal behavior, their viscosity and their miscibility with refrigerants, prototypes are 1,1,1,2-tetrafluoroethane and 2 H-heptafluoropropane.
  • the thermal stability of the esters is tested in accordance with DIN 51593 in a U-tube at 250/40 ° C and 96 h.
  • the oil-filled leg of the U-tube is set to 250 ° C and is in contact with the vapor phase of the refrigerant, which is condensed into the second leg and then set to 40 ° C.
  • the evaluation is done optically (oil discoloration).
  • an aqueous extract of the vapor phase is checked for fluoride ions by an ion-sensitive electrode.
  • a gas chromatographic analysis of the gas phase provides information about possible gaseous decomposition products of the ester or refrigerant.
  • the chromatogram is compared with that of a blank sample.
  • the viscosity of the esters is measured in an Ubbelohde viscometer at 40 ° C.
  • esters a defined amount of esters (approx. 0.2 to 3 g) are placed in a glass tube of approx. 10 ml content. After immersion in liquid nitrogen, depending on the concentration to be set, between 6 and 3 g of the refrigerant are condensed. The glass tube is then evacuated, sealed by melting and passing through a temperature range of -40 ° C to + 80 ° C with the mixture of certain compositions.
  • the separation point i.e. a point can be determined on the limit curve of the mixture diagram. The totality of the separation points found then gives the limit curve of the mixture gap.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Lubricants (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Claims (1)

  1. Utilisation d'esters d'acide phtalique, d'acide isophtalique ou d'acide téréphtalique et de monoalcools primaires, linéaires ou ramifiés de 4 à 20 atomes de carbone comme lubrifiant pour compresseurs frigorifiques qui fonctionnent avec des hydrocarbures sans chlore et partiellement fluorés comme fluide de travail.
EP91108312A 1990-06-09 1991-05-23 Utilisation d'esters d'acides aromatiques pour compresseur pour machines frigorifiques Expired - Lifetime EP0461435B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4018562 1990-06-09
DE4018562A DE4018562A1 (de) 1990-06-09 1990-06-09 Verwendung von estern aromatischer carbonsaeuren als schmiermittel fuer kaeltemittelverdichter

Publications (2)

Publication Number Publication Date
EP0461435A1 EP0461435A1 (fr) 1991-12-18
EP0461435B1 true EP0461435B1 (fr) 1994-08-24

Family

ID=6408142

Family Applications (1)

Application Number Title Priority Date Filing Date
EP91108312A Expired - Lifetime EP0461435B1 (fr) 1990-06-09 1991-05-23 Utilisation d'esters d'acides aromatiques pour compresseur pour machines frigorifiques

Country Status (6)

Country Link
EP (1) EP0461435B1 (fr)
JP (1) JPH0778229B2 (fr)
AT (1) ATE110408T1 (fr)
DE (2) DE4018562A1 (fr)
DK (1) DK0461435T3 (fr)
ES (1) ES2063403T3 (fr)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5452586A (en) * 1994-09-19 1995-09-26 Huls America, Inc. Method for flushing a refrigeration system
WO2000029520A1 (fr) * 1998-11-12 2000-05-25 Exxon Chemical Patents Inc. Compositions d'huiles lubrifiantes contenant des esters de phtalate
TW482761B (en) 1999-07-19 2002-04-11 New Japan Chem Co Ltd Dicarboxylic acid diester, a process for preparation thereof and refrigerator lubricating oil containing the diester
WO2001074977A2 (fr) * 2000-03-31 2001-10-11 Ici Americas Inc. Compositions lubrifiantes et de rinçage
AR113699A1 (es) * 2017-11-30 2020-06-03 Lubrizol Corp Lubricante de éster aromático para uso con refrigerantes con bajo potencial de calentamiento global
US20200024537A1 (en) * 2018-02-22 2020-01-23 Exxonmobil Research And Engineering Company Low viscosity low volatility benzoate monoester lubricating oil base stocks and methods of use thereof
JP2023073864A (ja) * 2021-11-16 2023-05-26 出光興産株式会社 冷凍機油組成物及び冷凍機用混合組成物

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2852470A (en) * 1954-10-15 1958-09-16 Gen Motors Corp Refrigeration composition
GB8806923D0 (en) * 1988-03-23 1988-04-27 Ici Plc Lubricants
ATE124438T1 (de) * 1988-12-06 1995-07-15 Idemitsu Kosan Co Vervendung eines specifischen polyalkylenglykol derivats als schmiermittel für kompressorkühlanlagen, verfahren zum schmieren und dieses derivat enthaltende kompressorkühlanlage.

Also Published As

Publication number Publication date
ES2063403T3 (es) 1995-01-01
ATE110408T1 (de) 1994-09-15
DE59102610D1 (de) 1994-09-29
DE4018562A1 (de) 1991-12-12
DK0461435T3 (da) 1994-09-19
JPH0778229B2 (ja) 1995-08-23
EP0461435A1 (fr) 1991-12-18
JPH04226193A (ja) 1992-08-14

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